The present invention relates to novel carbanilides, to a plurality of processes for their preparation and to their use for controlling plant and animal pests.
It is already known that numerous carboxamides have fungicidal properties (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313). The activity of these compounds is good, but in some cases leaves something to be desired.
This invention, accordingly, provides novel carbanilides of the formula 
in which
R represents halogen, nitro, cyano, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
m represents numbers 0, 1, 2, 3 or 4,
A represents a radical of the formula 
xe2x80x83in which
R1 represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R2 represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula 
xe2x80x83in which
R3 and R4 independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R5 represents halogen, cyano, alkyl having 1 to 4 carbon atoms or halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R6 and R7 independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R8 represents hydrogen, alkyl having 1 to 4 carbon atoms or represents halogen, or
A represents a radical of the formula 
xe2x80x83in which
R9 represents halogen, cyano, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms or represents halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R10 represents halogen, cyano, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R11 represents hydrogen, halogen, cyano, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms or represents halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R12 represents alkyl having 1 to 4 carbon atoms or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,
X1 represents a sulphur atom, represents SO, SO2 or xe2x80x94CH2, or
A represents a radical of the formula 
xe2x80x83in which
R13 represents alkyl having 1 to 4 carbon atoms or represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R14 represents halogen, cyano, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R15 and R16 independently of one another each represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms and
R17 represents hydrogen, halogen or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula 
xe2x80x83in which
R18 represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4 carbon atoms and
R19 represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R20 represents hydrogen, halogen, amino, cyano or alkyl having 1 to 4 carbon atoms and
R21 represents halogen, alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbons and 1 to 5 halogen atoms, or
A represents a radical of the formula 
xe2x80x83in which
R22 represents hydrogen or alkyl having 1 to 4 carbon atoms and
R23 represents halogen or alkyl having 1 to 4 carbon atoms, or
A represents a radical of the formula 
Q represents alkylene having 1 to 4 carbon atoms, alkenylene having 2 to 4 carbon atoms, alkinylene having 2 to 4 carbon atoms or a group of the formula 
xe2x80x83in which
R24, R25 and R26 independently of one another each represent hydrogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl having 2 to 4 carbon atoms or alkinyl having 2 to 4 carbon atoms, or
Q represents a group of the formula 
xe2x80x83in which
R27 and R28 independently of one another each represent hydrogen or alkyl having 1 to 4 carbon atoms,
Y represents an oxygen atom or represents S(O)r, where
r represents the numbers 0, 1 or 2, and
n and p independently of one another each represent the numbers 0, 1 or 2,
where the molecular moiety labelled (*) is in each case attached to the phenyl radical of the aniline moiety,
X represents oxygen or sulphur and
Z represents optionally substituted phenyl, optionally substituted naphthyl, optionally substituted anthracenyl or represents optionally substituted hetaryl.
Furthermore, it has been found that carbanilides of the formula (I) are obtained when
a) acyl halides of the formula 
xe2x80x83in which
A and X are each as defined above and
Hal represents halogen
are reacted with aniline derivatives of the formula 
xe2x80x83in which
Q, R, Z and m are each as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
b) carbanilide derivatives of the formula 
xe2x80x83in which
A, R, X and m are each as defined above and
X2 represents oxygen or sulphur,
are reacted with compounds of the formula 
xe2x80x83in which
R28, Z and p are each as defined above and
E represents a leaving group,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
c) carbanilide derivatives of the formula 
xe2x80x83in which
A, R, R27, X and m are each as defined above and
E1 represents a leaving group
are reacted with compounds of the formula 
xe2x80x83in which
R28, Z and p are each as defined above and
X3 represents oxygen or sulphur,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
d) carbanilide derivatives of the formula 
xe2x80x83in which
A, R, R27, X and m are each as defined above
are reacted with compounds of the formula 
xe2x80x83in which
R28, Z and p are each as defined above and
E represents a leaving group,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent or,
e) carbanilide derivatives of the formula 
xe2x80x83in which
A, R, R26, X and m are each as defined above
are reacted with hydroxylamine derivatives of the formula
H2Nxe2x80x94Oxe2x80x94Zxe2x80x83xe2x80x83(X)
xe2x80x83in which
Z is as defined above,
if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
Finally, it has been found that the novel carbanilides of the formula (I) are very suitable for use as pesticides. They have microbicidal properties and can be employed for controlling undesirable microorganisms both in crop protection and in the protection of materials. Additionally, they are suitable for controlling animal pests.
Surprisingly, the carbanilides of the formula (I) according to the invention have considerably better fungicidal activity than the constitutionally most similar prior-art carboxamides of the same direction of action.
The formula (I) provides a general definition of the carbanilides according to the invention.
R preferably represents fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety.
m preferably represents the numbers 0, 1, 2 or 3, where R represents identical or different radicals if m represents 2 or 3.
A preferably represents a radical of the formula 
xe2x80x83in which
R1 represents fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
R2 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or ethyl.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R3 and R4 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
R5 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R6 and R7 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
R8 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R9 represents fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms or represents halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R10 represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio or represents halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
R11 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio or represents halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of formula 
xe2x80x83in which
R12 represents methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
X1 represents a sulphur atom, represents SO, SO2 or xe2x80x94CH2xe2x80x94.
A furthermore preferably represents a radical of formula 
xe2x80x83in which
R13 represents methyl, ethyl or halogenoalkyl, having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R14 represents fluorine, chlorine, bromine, cyano, methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R15 and R16 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms and
R17 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R18 represents hydrogen, fluorine, chlorine, bromine, amino, cyano, methyl or ethyl and
R19 represents fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R20 represents hydrogen, fluorine, chlorine, bromine, amino, cyano, methyl or ethyl and
R21 represents fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms.
A furthermore preferably represents a radical of the formula 
xe2x80x83in which
R22 represents hydrogen, methyl or ethyl and
R23 represents fluorine, chlorine, bromine, methyl or ethyl.
A furthermore preferably represents a radical of the formula 
Q preferably represents alkylene having 1 to 3 carbon atoms, alkenylene having 2 or 3 carbon atoms, alkinylene having 2 or 3 carbon atoms or represents a group of the formula 
xe2x80x83in which
R24, R25 and R26 independently of one another each represent hydrogen, methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, alkenyl having 2 or 3 carbon atoms or alkinyl having 2 or 3 carbon atoms.
Q furthermore preferably represents a group of the formula 
xe2x80x83in which
R27 and R28 independently of one another each represent hydrogen, methyl or ethyl,
Y represents an oxygen atom or represents S(O)r where
r represents the numbers 0, 1 or 2 and
n and p independently of one another each represent the numbers 0, 1 or 2, where the molecular moiety labelled (*) is in each case attached to the phenyl radical of the aniline moiety.
X also preferably represents oxygen or sulphur.
Z preferably represents phenyl, naphthyl or anthracenyl, where each of these radicals may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, phenyl and phenoxy.
Z furthermore preferably represents hetaryl having 5 or 6 ring members and 1 to 3 heteroatoms, such as oxygen, sulphur and/or nitrogen, where each of the heterocycles may be mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, phenyl and phenoxy.
R particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethylthio, allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl.
m particularly preferably represents the numbers 0, 1, 2 or 3, where R represents identical or different radicals if m represents 2 or 3.
A particularly preferably represents a radical of the formula 
xe2x80x83in which
R1 represents fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and
R2 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or ethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R3 and R4 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R5 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R6 and R7 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R8 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R9 represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R10 represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy and
R11 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R12 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
X1 represents a sulphur atom, represents SO, SO2 or xe2x80x94CH2xe2x80x94.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R13 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R14 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R15 and R16 independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
R17 represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R18 represents hydrogen, fluorine, chlorine, bromine, amino, cyano, methyl or ethyl and
R19 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R20 represents hydrogen, fluorine, chlorine, bromine, amino, cyano, methyl or ethyl and
R21 represents fluorine, chlorine, bromine, methyl, ethyl trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
A furthermore particularly preferably represents a radical of the formula 
xe2x80x83in which
R22 represents hydrogen, methyl or ethyl and
R23 represents fluorine, chlorine, bromine, methyl or ethyl.
A furthermore particularly preferably represents a radical of the formula 
Q particularly preferably represents alkylene having 1 to 3 carbon atoms, alkenylene having 2 or 3 carbon atoms, alkinylene having 2 or 3 carbon atoms or represents a group of the formula 
R24, R25 and R26 independently of one another each represent hydrogen, methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl or propargyl.
Q furthermore particularly preferably represents a group of the formula 
R27 and R28 independently of one another each represent hydrogen, methyl or ethyl,
Y represents an oxygen atom or represents S(O)r, where
r represents the numbers 0, 1 or 2, and
n and p independently of one another each represent the numbers 0, 1 or 2, where the molecular moiety labelled (*) is in each case attached to the phenyl radical of the aniline moiety.
X also particularly preferably represents oxygen or sulphur.
Z particularly preferably represents phenyl, naphthyl or anthracenyl, where each of these radicals may be mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-butyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, phenyl and phenoxy.
Z furthermore particularly preferably represents pyrrolyl, furyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, pyridyl, pyrimidyl, pyrazinyl or pyridazinyl, where each of these radicals may be mono- or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, phenyl and phenoxy.
Using 3-difluoromethoxy-thiophene-2-carbonyl chloride and 2-(2-phenyl-ethen-1-yl)-aniline as starting materials, the course of the process (a) according to the invention can be illustrated by the equation below. 
Using 2-hydroxy-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide and 2,4-dimethyl-benzylchloride as starting materials, the course of the process (b) according to the invention can be illustrated by the equation below. 
Using 2-bromomethyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide and 4-chloro-thiophenol as starting materials, the course of the process (c) according to the invention can be illustrated by the equation below. 
Using 2-hydroxymethyl-1-methyl-3-trifluoromethyl-pyrazole-4-carboxanilide and 2,4-dimethylbenzyl chloride as starting materials, the course of the process (d) according to the invention can be illustrated by the equation below. 
Using 1-methyl-2-methylcarbonyl-3-trifluoromethylpyrazole-4-carboxanilide and O-phenyl-hydroxylamine as starting materials, the course of the process (e) according to the invention can be illustrated by the equation below. 
The formula (II) provides a general definition of the acyl halides required as starting materials for carrying out the process (a) according to the invention. In this formula, A and X each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals. Hal preferably represents fluorine, chlorine or bromine.
The acyl halides of the formula (II) are known or can be prepared by known methods (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313).
The formula (III) provides a general definition of the aniline derivatives required as reaction components for carrying out the process (a) according to the invention. In this formula Q, R, Z and m each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index.
The aniline derivatives of the formula (III) are known or can be prepared by known methods (cf. WO 93-11 117, EP-A 0 545 099, EP-A 0 589 301, EP-A 0 371 950 and EP-A 0 292 990).
Suitable acid binders for carrying out the process (a) according to the invention are all inorganic and organic bases which are customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or else ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). However, it is also possible to carry out the reaction without additional acid binder, or to use the amine component in an excess, so that it simultaneously acts as acid binder.
Suitable diluents for carrying out the process (a) according to the invention are all customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulphoxides, such as dimethylsulphoxide, or sulphones, such as sulpholane.
When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between 0xc2x0 C. and 120xc2x0 C., preferably between 10xc2x0 C. and 100xc2x0 C.
Both the process (a) according to the invention and the processes (b) to (e) according to the invention are generally carried out under atmospheric pressure. However, it is in each case also possible to carry out the reaction under elevated or reduced pressure.
When carrying out the process (a) according to the invention, generally 1 mol or else an excess of aniline derivative of the formula (III) and 1 to 3 mol of acid binder are employed per mole of acyl halide of the formula (II). However, it is also possible to employ the reaction components in other ratios. Work-up is carried out by customary methods. In general, the reaction mixture is admixed with water, and the organic phase is separated off and, after drying, concentrated under reduced pressure. The residue that remains may, if appropriate, be freed of any impurities that may still be present by customary methods, such as chromatography or recrystallization.
The formula (IV) provides a general definition of the carbanilide derivatives required as starting materials for carrying out the process (b) according to the invention. In this formula A, R, X and m preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index. X2 also preferably represents oxygen or sulphur.
The carbanilide derivatives of the formula (IV) are known or can be prepared by known methods. Thus, compounds of the formula (IV) are obtained when acyl halides of the formula 
in which
A, X and Hal are each as defined above
are reacted with amino-phenols or aminothiophenols of the formula 
in which
R, X2 and m are each as defined above,
if appropriate in the presence of an acid binder, such as, for example, potassium carbonate or a tertiary amine, and if appropriate in the presence of an inert organic diluent, such as, for example, toluene, at temperatures between 20xc2x0 C. and 150xc2x0 C.
The amino-phenols or aminothiophenols of the formula (XI) required as reaction components for carrying out the above process are known or can be prepared by known methods.
The formula (V) provides a general definition of the compounds required as reaction components for carrying out the process (b) according to the invention. In this formula, R28, Z and p each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index. E preferably represents chlorine, bromine, iodine, methylsulphonyloxy, tolylsulphonyloxy or a radical of the formula R29xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94 or R29xe2x80x94Oxe2x80x94COxe2x80x94Oxe2x80x94, in which R29 represents alkyl having 1 to 4 carbon atoms and preferably represents methyl or ethyl.
The compounds of the formula (V) are also known or can be prepared by known methods.
Suitable acid binders for carrying out the process (b) according to the invention are all inorganic or organic bases which are customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium ten-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Suitable diluents for carrying out the process (b) according to the invention are all customary inert organic solvents. Preference is given to using all those diluents which have already been mentioned in connection with the description of the process (a) according to the invention as being preferred.
When carrying out the process (b) according to the invention, the reaction temperatures may also be varied within a relatively wide range. In general, the process is carried out at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C., preferably between xe2x88x9210xc2x0 C. and +120xc2x0 C.
When carrying out the process (b) according to the invention, generally 1 to 2 mol of a compound of the formula (V) and, if appropriate, an equivalent amount or else an excess of acid binder are employed per mole of carbanilide derivative of the formula (IV). Work-up is carried out by customary methods. In general, the reaction mixture is admixed with water and the organic phase is separated off and, after drying, concentrated under reduced pressure. If a water-miscible solvent is employed for carrying out the reaction, the desired product is generally obtained as a solid on dilution of the reaction mixture with water. In this case, the isolation is generally carried out by simple filtering off with suction. The product which is obtained in each case can, if appropriate, be freed of any impurities that may still be present by customary methods, such as chromatography or recrystallization.
The formula (VI) provides a general definition of the carbanilide derivatives required as starting materials for carrying out the process (c) according to the invention. In this formula, A, R, R27, X and m each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index. E1 preferably represents chlorine, bromine, iodine, methylsulphonyloxy, tolylsulphonyloxy or a radical of the formula R29xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94 or R29xe2x80x94Oxe2x80x94COxe2x80x94Oxe2x80x94 in which R29 represents alkyl having 1 to 4 carbon atoms and preferably represents methyl or ethyl.
The carbanilide derivatives of the formula (VI) are known or can be prepared by known methods.
The formula (VII) provides a general definition of the compounds required as reaction components for carrying out the process (c) according to the invention. In this formula, R28, Z and p each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index. X3 also preferably represents oxygen or sulphur.
The compounds of the formula (VIII) are also known or can be prepared by known methods.
Suitable acid binders for carrying out the process (c) according to the invention are all inorganic and organic bases which are customary for such reactions. Preference is given to using all those acid acceptors which have already been mentioned in connection with the description of the process (b) according to the invention as being preferred.
Suitable diluents for carrying out the process (c) according to the invention are water and all customary inert, organic solvents. Preference is given using aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamides; esters such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propinole, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
When carrying out the process (c) according to the invention, the reaction temperatures may also be varied within a relatively wide range. In general, the process is carried out at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C., preferably between xe2x88x9210xc2x0 C. and +120xc2x0 C.
When carrying out the process (c) according to the invention, generally 1 to 2 mol of a compound of the formula (VII) and, if appropriate, an equivalent amount or else an excess of acid binder are employed per mole of carbanilide derivative of the formula (VI). Work-up is carried out by customary methods.
The formula (VIII) provides a general definition of the carbanilide derivatives required as starting materials for carrying out the process (d) according to the invention. In this formula, A, R, R27, X and m each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index.
The carbanilide derivatives of the formula (VIII) are known or can be prepared by known methods.
Suitable acid binders for carrying out the process (d) according to the invention are all inorganic and organic bases which are customary for such reactions. Preference is given to using all those acid acceptors which have already been mentioned as being preferred in connection with the description of the process (b) according to the invention.
Suitable diluents for carrying out the process (d) according to the invention are all customary inert organic solvents. Preference is given to all those diluents which have already been mentioned as being preferred in connection with the description of the process (a) according to the invention.
When carrying out the process (d) according to the invention, the reaction temperatures may also be varied within a relatively wide range. In general, the process is carried out at temperatures between xe2x88x9220xc2x0 C. and +150xc2x0 C., preferably between xe2x88x9210xc2x0 C. and +120xc2x0 C.
When carrying out the process (d) according to the invention, generally 1 to 2 mol of a compound of the formula (V) and, if appropriate, an equivalent amount or else an excess of acid binder are employed per mole of carbanilide derivative of the formula (VIII). Work-up is carried out by customary methods.
The formula (IX) provides a general definition of the carbanilide derivatives required as starting materials for carrying out the process (e) according to the invention. In this formula, A, R, R26, X and m each preferably have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for these radicals or this index.
The carbanilide derivatives of the formula (IX) are known or can be prepared by known methods.
The formula (X) provides a general definition of the hydroxylamine derivatives required as reaction components for carrying out the process according to the invention. In this formula, Z preferably has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for this radical.
The hydroxylamine derivatives of the formula (X) are known or can be prepared by known methods.
Suitable catalysts for carrying out the process (e) according to the invention are all acidic reaction promoters which are customary for such reactions. Preference is given to using hydrogen chloride, sulphuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methane sulphonic acid, trifluoromethanesulphonic acid, toluenesulphonic acid, boron trifluoride (also as etherate), boron tribromide, aluminium trichloride, titanium tetrachloride, tetrabutylorthotitanate, zinc chloride, iron(III) chloride, antimony pentachloride, acidic ion exchangers, acidic alumina and acidic silica gel.
Suitable diluents for carrying out process (e) according to the invention are all inert organic solvents which are customary for such reactions. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; furthermore halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane and also nitrites, such as n- or i-butyronitrile or benzonitrile.
When carrying out the process (e) according to the invention, the reaction temperatures can also be varied within a relative wide range. In general, the process is carried out at temperatures between 0xc2x0 C. and 150xc2x0 C., preferably between 20xc2x0 C. and 120xc2x0 C.
When carrying out the process (e) according to the invention, generally 1 to 2 mol of hydroxylamine derivative of the formula (X) are employed per mole of carbanilide derivative of the formula (IX). Work-up is carried out by customary methods.
The compounds according to the invention have a potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
Fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bactericides can be employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Some pathogens causing fungal and bacterial diseases which come under the generic names listed above are mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; 
Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; 
Erwinia species, such as, for example, Erwinia amylovora; 
Pythium species, such as, for example, Pythium ultimum; 
Phytophthora species, such as, for example, Phytophthora infestans; 
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; 
Plasmopara species, such as, for example, Plasmopara viticola; 
Bremia species, such as, for example, Bremia lactucae, 
Peronospora species, such as, for example, Peronospora pisi or P. brassicae; 
Erysiphe species, such as, for example, Erysiphe graminis; 
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; 
Podosphaera species, such as, for example, Podosphaera leucotricha; 
Venturia species, such as, for example, Venturia inaequalis; 
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus; 
Puccinia species, such as, for example, Puccinia recondita; 
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum 
Tilletia species, such as, for example, Tilletia caries; 
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; 
Pellicularia species, such as, for example, Pellicularia sasakii; 
Pyricularia species, such as, for example, Pyricularia oryzae; 
Fusarium species, such as, for example, Fusarium culmorum; 
Botrytis species, such as, for example, Botrytis cinerea; 
Septoria species, such as, for example, Septoria nodorum; 
Leptosphaeria species, such as, for example, Leptosphaeria nodorum; 
Cercospora species, such as, for example, Cercospora canescens; 
Alternaria species, such as, for example, Alternaria brassicae; and
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides. 
The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil.
The active compounds according to the invention can be employed particularly successfully for controlling diseases in viticulture and fruit and vegetable growing, such as, for example, against Venturia, Podosphaera, Phytophthora and Plasmopara species. They are also very successfully used for controlling rice diseases, such as, for example, Pyricularia species.
In the protection of materials, the compounds according to the invention can be employed for protecting industrial materials against infection with, and destruction by, undesired microorganisms.
Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry. For example, industrial materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be adhesives, sizes, paper and board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with, or destroyed by, microorganisms. Parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials which may be mentioned within the scope of the present invention are preferably adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids, particularly preferably wood.
Microorganisms capable of degrading or changing the industrial materials which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
Microorganisms of the following genera may be mentioned as examples:
Alternaria, such as Alternaria tenuis, 
Aspergillus, such as Aspergillus niger, 
Chaetomium, such as Chaetomium globosum, 
Coniophora, such as Coniophora puetana, 
Lentinus, such as Lentinus tigrinus, 
Penicillium, such as Penicillium glaucum, 
Polyporus, such as Polyporus versicolor, 
Aureobasidium, such as Aureobasidium pullulans, 
Sclerophoma, such as Sclerophoma pityophila, 
Trichoderma, such as Trichoderma viride, 
Escherichia, such as Escherichia coli, 
Pseudomonas, such as Pseudomonas aeruginosa, 
Staphylococcus, such as Staphylococcus aureus. 
The active compounds according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in horticulture in the protection of stored products and of materials, and in the hygiene or veterinary medicine sector, and have good plant tolerance and favourable toxicity to warm-blooded animals. The compounds are active against normally sensitive and resistant species and against pests in all or some stages of development. The abovementioned animal pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber. 
From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec.
From the order of the Symphyla, for example, Scutigerella immaculata. 
From the order of the Thysanura, for example, Lepisma saccharina. 
From the order of the Collembola, for example, Onychiurus armatus. 
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Dermaptera, for example, Forficula auricularia. 
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example, Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. 
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderrna spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. 
From the order of the Siphonaptera, for example, Xenopsylla cheopis and Ceratophyllus spp.
From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. 
From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.
The phytoparasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp.
Depending on their particular physical and/or chemical properties, the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The active compounds according to the invention can be used as such or in their formulations also mixed with known fungicides, bactericides, acaricides, nematicides or insecticides in order thus, for example, to widen the spectrum of action or to prevent development of resistance. In many cases, synergistic effects are achieved, i.e. the activity of the mixture exceeds the activity of the individual components.
Examples of co-components in mixtures are the following compounds:
Fungicides:
aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticdin-S, bromuconazole, bupirimate, buthiobate,
calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,
debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,
edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
guazatine,
hexachlorobenzene, hexaconazole, hymexazole,
imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, isovaledione,
kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
quinconazole, quintozene(PCNB),
sulphur and sulphur preparations,
tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
uniconazole,
validamycin A, vinclozolin, viniconazole,
zarilamide, zineb, ziram and also
Dagger G,
OK-8705,
OK-8801,
2xe2x80x2,6xe2x80x2-dibromo-2-methyl-4xe2x80x2-trifluoromethoxy-4xe2x80x2-trifluoro-methyl-1,3-thiazole-5-carboxanilide,
2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,
2-aminobutane,
2-phenylphenol (OPP)
8-hydroxyquinoline sulphate,
cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,
(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,
xcex1-(2,4-dichlorophenyl)-xcex2-methoxy-xcex1-methyl-1H-1,2,4-triazole-1-ethanol,
xcex1-(1,1-dimethylethyl)-xcex2-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,
1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,
bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,
(E)-xcex1-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,
9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,
O-methyl S-phenyl phenylpropylphosphoramidothioate,
N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,
1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,
N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,
1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinone,
1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,
1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole, methanetetrathiol sodium salt
2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,
N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-Nxe2x80x2-methoxy-methaneimideamide,
xcex1-(5-methyl-1,3-dioxan-5-yl)-xcex2-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,
1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,
N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,
N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,
N-formyl-N-hydroxy-DL-alanine-sodium salt,
N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,
4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,
2-chloro-N-(2,6-dimethylphenyl)-N-isothiocyanatomethyl)-acetamide,
ethyl [(4-chlorophenyl)-azo]-cyanoacetate,
N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,
N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,
methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,
3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,
2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,
spiro[2H]-1-benzopyrane-2,1xe2x80x2(3xe2x80x2H)-isobenzofuran]-3xe2x80x2-one,
methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,
potassium hydrogen carbonate,
1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl)-1H-imidazole,
1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,
2-bromo-2-(bromomethyl)-pentanedinitrile,
2-[[6-deoxy-4-O-(4-O-methyl-xcex2-D-glycopyranosyl)-xcex1-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
methyl 1-(2,3-dihydro-2,2-dimethy-1H-inden-1-yl)-1H-imidazole-5-carboxylate,
2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,
O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
xcex1-(2,4-dichlorophenyl)-xcex2-fluoro-xcex2-propyl-1H-1,2,4-triazole-1-ethanol,
3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,
S-methyl 1,2,3-benzothiadiazole-7-carbothioate,
N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,
3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,
8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4,5]decane-2-methaneamine,
2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,
N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insecticides/Acaricides/Nematicides:
abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, betacyluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulphoton,
edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos,
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
HCH, heptenophos, hexaflumuron, hexythiazox,
imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,
lambda-cyhalothrin, lufenuron,
malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
naled, NC 184, NI 25, nitenpyram,
omethoate, oxamyl, oxydemethon M, oxydeprofos,
parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
quinalphos,
RH 5992,
salithion, sebufos, silafluofen, sulfotep, sulprofos,
tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,
vamidothion, XMC, xylylcarb, zetamethrin.
It is also possible to admix other known active compounds, such as herbicides, fertilizers and growth-promoting substances.
The active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, spreading, foaming, brushing on and the like. It is further possible to apply the active compounds by the ultra-low volume method or to inject the active compound formulation, or the active compound itself, into the soil. The seed of the plants can also be treated.
In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
In the treatment of seed, amounts of active compound of from 0.001 to 50 g, preferably 0.01 to 10 g, are generally required per kilogram of seed.
In the treatment of the soil, active compound concentrations of from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight, are required at the site of action.
The compositions used for the protection of industrial materials generally comprise an amount of 1 to 95%, preferably 10 to 75%, of the active compounds.
The use concentrations of the active compounds according to the invention depend on the species and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal rate of application can be determined by test series. In general, the use concentrations are in the range from 0.001 to 5% by weight, preferably 0.05 to 1.0% by weight, based on the material to be protected.
The activity and the activity spectrum of the active compounds which are to be used according to the invention in the protection of materials, or of the compositions, concentrates or quite generally formulations which can be prepared therefrom, can be increased by adding, if appropriate, further compounds having antimicrobial activity, fungicides, bactericides, herbicides, insecticides or other active compounds for widening the activity spectrum or for achieving particular effects, such as, for example, the additional protection against insects. These mixtures may have a wider spectrum of activity than the compounds according to the invention.
Likewise, when used against animal pests the compounds according to the invention may be present in commercial formulations, and in the use forms prepared from these formulations as a mixture with synergists. Synergists are compounds which increase the activity of the active compounds, without it being necessary for the added synergist to be active itself.
The content of active compound of the use forms prepared from the commercial formulations can be varied within wide ranges. The active compound concentration in the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
Application is carried out in a customary manner adapted to the use forms.
The preparation and the use of the compounds according to the invention is illustrated by the examples below.